


Are You In?

by sephirothflame



Series: you belong with me (the doorman 'verse) [4]
Category: Shadowhunters (TV)
Genre: Alternate Universe, Blow Jobs, Choking, F/M, First Time, Light BDSM, M/M, Threesome - F/M/M, Voyeurism
Language: English
Status: Completed
Published: 2017-03-07
Updated: 2017-03-07
Packaged: 2018-09-30 07:56:39
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 9,184
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10158065
Author URL: https://archiveofourown.org/users/sephirothflame/pseuds/sephirothflame
Summary: Interlude: The disastrous night of meeting the family, Isabelle has a plan on how they can mend bridges and turn the night around for the better. Simon isn't sure he agrees since it's literally his ass on the line.This is gratuitous pornso it can be read as a standalone.





	

**Author's Note:**

> I feel like I need to say this was written before 2.10 and Raphael's coming out, so to speak. Since this is an alternate universe and not main storyline for this universe, I'm going to go ahead and post it anyway.
> 
> Raphael is gay. Isabelle watches. There is choking and Master/Pet endearments and virgin ass pounding. It's not entirely Safe, Sane, Consensual in the sense that they did not speak about mutual wants/desires before staring though every act is consensual. A few mentions of past Simon/Maureen and mentions of recreational drug use. I really don't know if I need to warn for anything else and I'm sorry if I missed something.
> 
> As always, this is for Max.

“So,” Isabelle says, “what do you do for a living?”

She smells like vanilla and something Simon can’t quite place and he has a hard time keeping his gaze on her face. “I work at Babylon Towers with your brother?”

Isabelle reaches out and taps Simon’s nose. “Not you, sweetie.”

Simons’ heart deflates but at least Raphael doesn’t look that interested in her. She stands between them, her back to the bar and her chest pushed out, and Raphael has the audacity to look more interested in his Corona. Simon would kill for that kind of attention.

“I’m not looking for a sugar baby,” Raphael says, frowning slightly when he looks at her.

“Wow,” Isabelle says, but she doesn’t sound truly offended. She looks at Simon and winks. “Is he always this grumpy?”

“To be honest, I barely know him,” Simon says. He rubs the back of his neck and sips the margarita Isabelle ordered him. It’s watermelon and he could happily drown in it. “He likes to visit the Towers after the front doors are  _ buzz in _ only and he feels the need to yell at me every single time.”

“Because it’s a stupid practice,” Raphael says. “What if the residents come back while you’re off smoking pot out back?”

“I  _ never _ get high and leave the desk unattended,” Simon says, affronted. “Eric usually covers my breaks for me and that is literally written into the schedule. Besides, it’s a  _ security feature _ .” He makes air quotes with his hands and Raphael scowls at him.

“It’s stupid,” Raphael says, eventually.

“And if your boy Magnus liked you, he could hook you up with one of the  _ swipe and go _ cards we use for the residents to come in on their own, but he clearly doesn’t,” Simon says. He shrugs and tries to feign indifference but it is not a thing he’s good at. “I bet Alec has one.”

Raphael stares at Simon like maybe he didn’t know that was an option. “I’m going to murder him.”

“There, there,” Isabelle says, patting Raphael’s arm. She sips her own drink and smiles sweetly while Raphael scowls at her. “I think it’s time we change the subject.”

“Right,” Simon says, nodding his head in agreement. “Talking about work is the last thing I want to do on my day off. What did you have in mind?”

Raphael looks between the two of them like he’s not quite sure why he’s associating with them, but he makes no move to leave. He knocks back his beer and orders another and Simon wonders if he can slip his drink on Raphael’s bill or if he’s going to have to pray he has enough on his bank card.

“I think we should talk about the possibility of a threesome,” Isabelle says casually.

Simon chokes on his drink and the margarita burns worse than hell coming out of his nose. He feels his face turn red as Isabelle laughs at him, patting his back until he can breathe again. It’s Raphael who hands him a napkin and Simon is only a little surprised.

“With who?” Simon asks, coughing.

Isabelle looks at Simon like he’s something small and adorable that needs coddled and Simon doesn’t hate it as much as when Clary gives him the very same look. “I think you should go ask my brother if you can sleep with him and his boyfriend, Simon.” She rolls her eyes and grins. “Obviously I mean the three of us.”

“I have absolutely no interest in women,” Raphael deadpans.

“Then you can fuck Simon while I watch,” Isabelle says. She makes it sound so obvious and Simon would agree, except he’s the one being volunteered to take it up the ass. “You don’t strike me as a bottom.”

“Do I get a say in this?” Simon asks, his voice breaking. He’s never had sex with a man before. He’s only been with one girl and it’s usually when they’re drunk and she normally reminds him that it was a mistake each and every time it happens. Maureen is a good friend and a great lead singer but as a lover she’s terrible for his ego. “I’ve never had anything in my butt.”

“We’ll be gentle with you,” Isabelle says soothingly.

“Speak for yourself,” Raphael says. He presses the mouth of his bottle against his lips but it does nothing to hide his smirk. “I don’t do gentle.”

“I suddenly wish I could be your sugar baby,” Isabelle says. She stands up straight and touches the patch of skin just below Raphael’s throat. “You could totally pay off my student loans and let me Domme boys like Simon with you.”

“No,” Raphael says.

Isabelle pouts.

“You could pay off my student loans, if you preferred,” Simon offers. He’s too terrified to check the balance due so far, but he has until he graduates to rack the number up higher and figure out how to deal with it then. “What are you going to school for?”

“Forensic anthropology,” Isabelle says. “You?”

“Accounting,” Simon admits. He gestures at Isabelle vaguely. “Your degree definitely sounds both more fun and way more complicated. And more expensive. You definitely deserve the sugar baby money.”

“No one is getting sugar baby money,” Raphael says, exasperated.

“You haven’t even told us what you do,” Isabelle says. She strokes Raphael’s chest slowly and pops the first button of his shirt. She smiles sweetly when he narrows his eyes. “My guess is, if you’re friends with Magnus, you’re probably in the property management field as well?”

“I own a hotel and co-own a club,” Raphael says. He curls his fingers around Isabelle’s wrist when she reaches for the next button on his shirt. He quirks an eyebrow but says nothing.

“Do either of these places have names?” Simon asks. “You know, so I can come harass you with stupid shit night after night when you’re trying to work.”

“Be nice,” Isabelle says. She pulls her wrist from Raphael’s grip and he lets her. She drains her margarita and sets it on the bar behind her before brushing Simon’s bangs out of his face. “You don’t think he has potential?”

“To annoy me? Yes, he has plenty,” Raphael says. He’s watching them both with an intense focus that makes Simon want to squirm.

“I mean it,” Isabelle says, smiling wickedly. Her thumb traces Simon’s lower lip, barely brushing against his skin. Almost instinctively, he parts his lips for her. “Imagine rubbing the head of your dick against his pretty lips before you fuck his face.”

Raphael cants his head ever so slightly, like maybe he’s considering Isabelle’s words. Or he’s trying to see the madness from her point of view, which is what Simon’s doing, because he’s pretty sure he’s not the one over here with blowjob lips.

Isabelle’s touch drops to Simon’s chest, her fingertips barely skimming along his skin as she pushes his shirt slightly off center. “You could leave a love bite right here. Look how pale he is. A good hickie will last for days on his complexion.” Her fingertips skim across his throat. “You said you like it rough? Maybe Simon would even let you choke him. Think about the bruises  _ that _ would leave.”

“Interesting,” Raphael says. He’s staring at Simon intently and suddenly this threesome joke looks like it’s becoming a lot more serious.

Simon licks his lips and tries to think of anything to say in his defense.  _ No, you absolutely are not choking me _ is the first thing that comes to mind, but he can’t bring himself to say it. Maybe it’s the tequila talking, but he’s low key interested in what that would feel like. Simon whimpers.

“See!” Isabelle says, beaming. She looks back at Raphael like the cat who caught the canary. Maybe Raphael isn’t the one that Simon needs to be worried about tonight. “He would totally let you do it.”

Raphael makes a show of pulling his sleeve back enough to check his watch. “I suppose,” he says, languidly. He touches the small of Isabelle’s back. “Go get your purse from your brother, then.”

Isabelle kisses Raphael’s cheek and there’s no bright red transfer of her lipstick. “Yes!”

“I can’t believe this is happening,” Simon says, spinning his barstool to stare at the accumulation of their bottles and glasses. Definitely enough between the three of them for this to be a very bad idea. “So, I hate to be that guy, but…”

Raphael  _ shhs _ him like he’s a child and pulls out a black credit card to pay off their tab. “Have you ever given head before?”

Simon shakes his head.

“When I ask you a question, I expect a  _ verbal _ answer,” Raphael says, coolly.

“Are you going to  _ 50 Shades _ this? Because I’m pretty sure that’s textbook abusive behaviour,” Simon says. At Raphael’s questioning look, Simon flushes. “I live with my sister and my mom and they both read a lot.”

“Have you ever given a blowjob or not?” Raphael repeats.

“Oh, no,” Simon says. He relaxes slightly. “I did highjack with Eric once, but that’s the closest I’ve ever been to having another penis near me. Sexually speaking, anyway. I’m sure other penises have been closer to me relatively speaking, but they’ve always been clothed.”

Isabelle’s arms wrap around Simon’s waist from behind. Her chin doesn’t even come to his shoulder and he’s sitting down. “Simon, don’t say anything to make Raphael regret this before we see his penis.”

“I already regret this,” Raphael says.

 

* * *

They end up at a hotel with a view of the Brooklyn Bridge, because Simon definitely can’t have a threesome at home and Isabelle claims her bed isn’t big enough. Raphael doesn’t even offer and tells them  _ no, I don’t own this hotel _ before they even get the chance to ask.

Simon would be affronted but even in the middle of the night the view from their bedroom window is amazing. “How much does a place like this even cost?”

“More than you make a week, probably,” Raphael says, sitting in one of the chairs casually and crossing his legs.

Isabelle and Simon share a look and Simon rolls his eyes. He’s not going to let it get to him when he’s already stressing out about being here in the first place. Isabelle’s arms wrap around his waist and Simon smiles as she presses a sweet kiss to his chin.

“So, how are we going to do this?” Isabelle asks, making Simon sway with her. Her playful smile is sweet enough to make Simon’s heart ache. “Do you want to fuck me while Raphael watches, do you want to be fucked by Raphael while I watch, or do you want to try and have both of us at once?”

“Would it do anything for you?” Simon asks, glancing over at Raphael. “I mean, if we had sex. Since you don’t like women.”

“Not really,” Raphael admits. “If she was forcing you to submit or pegging you, maybe, but just sex? No.”

Simon has no idea how someone could look at Isabelle and have no interest in being with her. She’s so small but feisty and her chest is very, very distracting. Simon wonders if it quivers like in the romance novels his mother and sister leave lying around. Not that Simon’s read them.

He looks at Isabelle. “But you could get off on watching Raphael and me?”

“Most women prefer gay porn to female-friendly straight porn,” Isabelle says. She shrugs her shoulders and smiles up at Simon. “Besides, I can always sit on your face when Raphael is done using you if I didn’t get off on my own.”

“You could definitely do that even if you do,” Simon says without thinking.

Isabelle makes an  _ aww  _ sound and touches his face gently. “You’re so sweet.” Her hand is surprisingly warm for how small it is and Simon tips his face into it to prolong the contact. “I think we should use the stoplight system.”

“Sounds reasonable,” Raphael says. He nods, mostly to himself, and looks at Simon expectantly. “You  _ are _ still interested in this?”

“I’m assuming  _ green _ means it’s a  _ go _ ?” Simon asks. At both Isabelle’s and Raphael’s confirmation, Simon nods his heads. He remembers Raphael’s statement about verbal answers. He licks his lips. “Yeah, green. Definitely green.”

Isabelle practically bounces across the room before dropping down into Raphael’s lap. She kisses his cheek and this time he just rolls his eyes at her. She lifts up a foot and wiggles it in Simon’s direction. “Help me with my pumps?”

Simon doesn’t know what else to do, so he crosses the room and kneels in front of her. Her legs are silky smooth and Simon is distracted by it. He could rub his face on her legs but he’s pretty sure that would probably be weird. He settles for trying to undo the little buckle on her right ankle before switching to the left. Her heels are probably at least four inches and Isabelle sighs happily when Simon tugs both of the gold pumps off her feet and sets them aside carefully so no one trips over them.

“Oh, that feels so much better,” Isabelle says. She leans back into Raphael’s body and grins. Simon’s pretty sure he can see her black panties from where her dress has been riding up her thighs and it’s even more distracting than her cleavage. “He is going to be so easy to train to be submissive.”

“I think so, yes,” Raphael agrees. He snaps to get Simon’s attention. “Strip. Put your clothes away  _ nicely _ .”

For a guy who supposedly doesn’t like women, Raphael isn’t objecting to Isabelle being in his lap. She hooks her knees on the outside of Raphael’s and Simon can  _ definitely _ see the black lace of Isabelle’s panties. Simon knows it’s rude to stare but holy crap this is his life.

Raphael clears his throat, his expression darkening and Simon scrambles to strip. He knows he was told to put his clothes away nicely but he can barely fold on the best of days so he hopes he at least gets an A for effort. He toes off his socks before he shimmies out of his boxers because nothing turns him off more in porn than someone’s ratty socks being on camera. He folds the last of his clothes and sets them on the pile he’s started and stands naked in front of Isabelle and Raphael.

“Not bad,” Isabelle says. She touches her blood red lips with blood red nails and eyes Simon from head to toe, her gaze lingering on his groin. “About what I expected.”

“It’s cold in here,” Simon says in his defense. He fights the urge to cover himself because Raphael’s gaze is still raking over him slowly. “It’s not even hard yet.”

“Oh, we’ll fix that,” Isabelle says with a wicked grin. “Why don’t you go ahead and get comfortable on the bed. Raphael and I need to talk for a minute.”

Simon wants to ask what the hell that means but Isabelle turns away from him. She brings her hand up to her face to hide her lips, like Simon could possibly know how to read them. Her murmuring is soft, just outside of what Simon can hear over the hum of the AC, and he figures he might as well obey her.

He wishes he’d thought to close the curtains as he drops back onto the bed, but the idea that someone out there could see him getting fucked turns him on in ways that surprise Simon. Despite the chill of the room and the fact he’s the only one completely exposed, Simons’s cock twitches against his stomach.

When he and Eric shared a blunt and loaded the van for the gig tonight, Simon had no idea this was where he was going to end up. He expected to have a drink or two with Clary and her new boyfriend and go to sleep in the twin bed he’s had for as long as he can remember. Simon doesn’t know if there was ever a time in his life where having a threesome was ever an option outside of porn fantasies.

Simon props himself up on his elbows when he catches Isabelle standing up out of the corner of his eyes. It’s only for Raphael to get up though and she drops back down immediately. There’s a hungry look in her eyes that Simon doesn’t know has ever been directed at him.

Raphael takes his time in getting undressed. He undoes each of the buttons on his shirt slowly before folding it neatly and setting it next to Simon’s messy stack of clothes. He pulls his overshirt over his head and does the same thing, but when he undoes his belt, he tosses it on the mattress.

Compared to the hard lines of muscle on Raphael’s body, Simon feels small and flabby. He knows he’s a little soft in the stomach, but it’s the hunger the pot brings that has done it to him. Simon really wants to lick Raphael’s abs and he wonders what those thick thighs and strong arms would feel like over him.

“Come here,” Raphael says, snapping Simon out of it.

Simon hesitates to obey, not entirely sure where this is going. He scoots down the length of the bed until he’s sitting on the edge in front of Raphael. He isn’t expecting the gentle way Raphael strokes his cheek or the soft pressure of his thumb on Simon’s lower lip. “Raphael?”

“You’re going to blow me,” Raphael says. His fingers end up in Simon’s hair and he tugs gently. He smirks when Simon moans. “I don’t expect you to make me come.”

“I might,” Simon says. He sincerely doubts it, but there’s a chance that he could be a natural at giving head. He’s certainly watched enough porn to understand the basics of it. Simon reaches for Raphael’s pants to pop the button and is surprised by the sharp, painful tug on his hair. He yelps.

“Did I give you permission to touch?” Raphael asks. He soothes Simon’s hair down and strokes his jaw.

“I knew this was going to be some  _ 50 Shades _ shit,” Simon says. He fights the urge to squirm away from the gentle massage of Raphael’s fingers. He doesn’t want to admit how much the manhandling and being bossed around is turning him on, but he can’t hide the way his cock is starting to swell when he’s completely naked. The only one completely naked. Simon swallows. “I’m sorry.”

“Good boy,” Raphael says. He pops the button on his slacks and drags his zipper down. He’s wearing black boxer briefs and he pulls his cock out slowly, already half hard. “Go on.”

“Give it a kiss,” Isabelle suggests. She makes it sound so innocent. Like she isn’t telling Simon to kiss Raphael’s cock before choking on it.

Simon would do as she asks, really, except he’s kind of fascinated by it. He’s never seen one up close and personal besides his own and Raphael isn’t circumcised. His foreskin stretches around the head of his cock and tapers off, soft and strange looking. It calls to Simon, begging to be touched and Simon wonders how much stretch it has. He’s seen things.

Honestly, Simon kind of digs it. It peels back easily enough, exposing the wet tip of Raphael’s cock, and he can pinch it closed with no effort. Simon thinks he could spend all day playing with Raphael’s penis if Raphael would let him.

“Simon.” An exasperated warning more than anything, but Simon can take a hint.

“I’m  _ Jewish _ ,” Simon says in his defense. He slips the tip of his thumb inside the warm opening of his foreskin and can feel the slick, velvety skin of Raphael’s slit. “I love it. Oh my god, Raphael, I have no idea how you don’t have your hand on yourself all of the time.”

“ _ Dios _ , just put it in your mouth before you change your mind,” Raphael groans.

Simon glances over at Isabelle. She’s made herself comfortable in the chair, at the perfect angle to view it all. The look she’s giving him makes Simon flush and he returns to the task at hand because he doesn’t want to disappoint either of them. Not when they’re this close to the main event.

Tentatively, Simon leans in and brushes his lips against Raphael's cock. It’s warm and surprisingly soft. Raphael’s scent is thick but heady. He smells even better than the cologne he wears and Simon wonders why he’d want to cover up his natural musk. Sighing softly, Simon licks his lips before kissing it again. This time, he parts his lips and lets his tongue drag against Raphael’s sensitive skin.

The fingers in Simon’s hair tighten and Raphael curses in Spanish.

Feeling braver, Simon presses wet kisses down the length of Raphael’s shaft. He’s pretty sure he can feel Raphael’s pulse when he sucks kisses onto the veiny underside and he’s positive he can feel Raphael’s cock swelling against his tongue. The head of Raphael’s cock pulls at his foreskin and Simon mouths his way back up to tongue that next.

“Simon,” Raphael says. He’s probably rolling his eyes that Simon has let his fascination bring him back, but he’s no objecting.

The first pulse of precome on Simon’s tongue is bitter. It’s not Simon’s favorite taste in the world but it could be worse, he supposes. He flattens his tongue and spreads it back on Raphael’s cock and he can feel Raphael moan above him. He may be inexperienced, but he’s definitely doing something right.

“It’s okay to use your hands, Simon,” Isabelle suggests. “You probably won’t be able to take more than the head and that’s okay. It’s your first time.”

Simon thinks he would blush if he had it in him. He wraps one hand around the base of Raphael’s cock and takes the head into his mouth. It stretches his jaw in a way he’s not used to and he has to concentrate on being mindful of his teeth. It’s not an awful experience. Simon thinks he could like it. He likes the sound of Raphael’s heavy breathing and how easy it is to tongue Raphael’s foreskin like this.

He sucks, because what else is he supposed to do with a cock in his mouth, and strokes his fist all way up to his lips. It’s a little dry, but Simon can feel the spit leaking from his mouth and he should be grossed out but this works in his favor. He jacks Raphael’s cock slowly as he tongues the head and moans. His jaw is going to kill him before he’s done, but fuck, does it feel good to have Raphael’s cock leaking against his tongue.

Raphael just lets Simon suck and stroke him at his own pace for an eternity, it feels like. His sighs are soft and occasionally Simon can feel his thighs tensing, but he’s nowhere close to getting off. His fingers tighten in Simon’s hair and he tugs gently. “Enough.”

The head of Raphael’s cock slips out of Simon’s mouth with an audible pop sound and there’s precome and spit connecting it to Simon’s lower lip. “Enough?”

“We’ll work on that,” Raphael says. He wipes Simon’s lower lip clean before pushing his thumb into Simon’s mouth. He sighs contently when Simon sucks. “On your hands and knees. Face the window.”

Doing that exposes his ass to Isabelle and Simon isn’t entirely sure the logistics of putting on a show that way, but he obeys. He stretches his jaw and savors the heady taste on his tongue while Raphael finishes stripping and pulls out the bottle of drugstore lube that they picked up on the way over. It smells like strawberries when Raphael pops the cap and he drizzles some of it directly on Simon’s puckered hole.

It’s cold and he can’t help the way he clenches and squirms. “Warn a guy, maybe?”

Raphael slaps Simon’s ass in warning. He moves to the side so that Isabelle can see and pours more lube on his fingers. He at least rubs his fingers together to warm them up before pressing one finger against Simon’s rim and rubbing gently. “Have you ever fingered yourself?”

“Once or twice,” Simon admits. He tries to will himself to relax but it all feels so foreign. “When I was in high school. ‘Cept I didn’t use lube because I didn’t realize that was a thing back then.”

“Silicone based lube for anal, unless you use a silicone toy,” Isabelle says. She’s out of Simon’s range of vision and it makes his heart race. He wonders what she looks like and if she’s turned on by the sight of Raphael working his fingertip into Simon’s body. He’s probably going to have to use all his fingers before Simon can take his cock. “Water based lube is great, but not so good for anal. You gotta pick your battles.”

“Like I’m going to go home and buy a dildo off of Amazon,” Simon huffs. Except, as Raphael manages to work a finger all the way into Simon, he thinks he just might. Anything to make this process easier. Raphael had said  _ we’ll work on that  _ like he was open to the possibility of this happening again.

“I can give you a list of recommendations,” Isabelle says. Simon knows she’s teasing, but he might just take her up on it. “I bought one for my brother, but I think it’s still unopened under his bed.”

“Well, he does have a boyfriend now,” Simon says. His breath catches as Raphael starts to pump his finger slowly. It feels odd. Not bad, per se. He can feel the way his body wants to pull Raphael’s finger deeper each time he pushes in and he wonders what it’ll feel like when he has Raphael’s cock inside of him instead.

“You’re still allowed to fuck yourself with a dildo if you have a boyfriend,” Isabelle says with a laugh.

Raphael reaches under Simon and pinches at his nipple. He doesn’t apologize when Simon yelps and presses a second finger against Simon’s rim while he’s distracted. “Relax, Simon.”

Simon wants to say something sassy and in return but nothing comes to mind. He’s too distracted by the press of a second finger inside of him and the way his cock is throbbing between his legs. He’s not sure if he’s supposed to be this turned on by the fingering portion of tonight but he definitely is. This feels way better than the few times he’s tried to do it to himself.

“If you’re going to be a bossy kind of guy, can I call you  _ Sir _ ?” Simon asks, He clenches has ass around Raphael’s fingers experimentally and groans. “Because I could do  _ Daddy _ but I gotta warn you, I’m not that into it.”

“What’s wrong with my name?” Raphael huffs.

“I’m with Simon,” Isabelle says. “ _ Sir _ is way kinkier. But only if you call me  _ Mistress _ .”

“I can’t call Raphael  _ Sir  _ and you  _ Mistress _ ,” Simon says, shaking his head. “That’s like calling him  _ private  _ and you  _ general _ . Not that you don’t deserve to be a Queen in this metaphor. But it would make you General Organa.”

“I guess you can call him  _ Master _ ?” Isabelle suggests.

Raphael sinks a third finger into Simon’s ass without warning. It makes Simon cry out and push his ass back against Raphael’s fist for more, because holy  _ fuck _ , the stretch and burn is starting to feel good. Raphael’s fingers pump into Simon a little harder.

“I’m guessing Raphael is on board with being  _ Master _ , then?” Isabelle says with a laugh.

Simon is very much on board with calling him  _ Master _ . He pants heavily and rocks his hips back to meet the slow, deep thrusts of Raphael’s fingers. “Master,” he says, experimentally. He likes the way it sounds on his tongue and the way Raphael’s fingers get a little rougher with him.

“Both of you need Jesus,” Raphael says, but it’s not an objection. He pumps his fingers into Simon slow and deep, dragging against Simon’s prostate with every push. Raphael pushes harder and Simon chokes back a moan.

“I think you’re going to make him come before you even fuck him,” Isabelle says. She sounds oddly amused at Simon’s torture.

“That was the plan,” Raphael says. His fingers twist and spread, stretching Simon as they move inside of him. They’re wonderful and Simon never, ever wants them to stop. He will sit on Raphael’s fingers for the rest of his life. “Go ahead and touch yourself, Pet.”

It takes Simon’s brain a minute to realize what Raphael is saying to him. The endearment makes him blush, oddly intimate for how downright dirty this entire situation is, and Simon loves it. Like his heart thuds in his chest he wants to hear it again kind of love. Not fell in love with the first guy to finger him love, that would be ridiculous. 

Dropping to his elbows, Simon reaches between his thighs and curls his fingers around his cock. It throbs in his hand, hot and swollen, and Simon strokes himself slowly. He knows for a fact it’s not going to take much for him to get off, not with the way Raphael’s fingers are fucking inside of him. Simon spreads the precome leaking from his cock down the length of his his shaft and whimpers.

“He’s going to be such a good sub for someone, some day,” Isabelle says, awed. “Oh, I wish I had time to take you home and train you between classes, Simon.”

Simon has no idea what that means and he really doesn’t want to think about it. The idea that Alec could see Simon in a situation even remotely like this makes Simon’s cock pulse wetly over his fingertips, and he bites his forearm to keep from screaming. He pushes back against Raphael’s fingers, riding them hard while he rides out his orgasm, but it’s not enough.

Even when Simon is panting and trembling, it’s not enough. He doesn’t want Raphael’s fingers, he wants his cock. He wants to be speared open and fucked hard. He wants Raphael to hold him down and take what he wants and needs from Simon and to be  _ used _ .

It should terrify him. Simon has no idea where any of these desires came from or why they’re so intense, but he needs them. He needs them so badly he can feel tears prickling the corners of his eyes and he chokes back a sob. “ _ Master _ .”

Raphael’s fingers stop working inside him, but he doesn’t pull them out. His free hand strokes down Simon’s spine gently, reassuringly. “It’s going to hurt at first.”

“I know,” Simon says. It’s true. He’s not dumb. Just because he’s never actually had a cock in him doesn’t mean he’s not aware that having one splitting him open isn’t going to ache. Simon wants that ache though and an entire community can’t be wrong about it feeling just as good as it hurts.

Raphael says something to Isabelle, but Simon’s brain can’t register the words. It takes him longer than he’s willing to admit to realize they’re speaking Spanish, but the slow drag of Raphael’s fingers inside of him is incredibly distracting. His body is too lax and he’s too sore to concentrate to pick out any of the words at all.

Eventually, Isabelle asks, “do you need to take a break Simon? Do you want a glass of water?”

“I’m good,” Simon says. He can’t twist to face her when Raphael’s fingers are still inside him, but he can glance over his shoulder, almost. He tries to smile but ends up choking on a moan when Raphael rubs his prostate. “I’m not the one and done type, I’m fine.”

“That’s very reassuring,” Raphael says. Slowly, he pulls his fingers out of Simon and wipes his sticky fingers on the back of Simon’s thigh. “You’re going to be on top, for now.” It’s not a question but then Simon guesses he wasn’t expecting it to be.

Raphael leans against the headboard and waits. His cock is hard, leaking against his abs, and Simon really wants to put it back in his mouth. Raphael rolls a condom down the length of his cock slowly, pinching the tip and rolling it down in one easy motion. He makes it look easy, like he has casual sex with strangers all the time that he is in absolutely no rush to bang.

“Could you,” Simon starts, but he doesn’t know how to ask. He picks up the tube of lube and he’s kind of amazed how much is already missing. It’s kind of touching that Raphael was that worried about stretching Simon out, but also Simon wonders how much his ass is going to itch in the morning once it’s all dry.

“Could I what, Pet?” Raphael asks. He takes the bottle when it’s offered, but he makes no move to do anything with it. His eyes are dark and intense and it takes everything in Simon to maintain contact and not stare at his lap helplessly.

Simon’s face flushes to the point he can feel his ears getting warm. “Could you please lube up your cock?”

“I could,” Raphael says. He waits.

Isabelle stifles a laugh and Simon huffs. He feels like he’s in grade school, being forced to learn the difference between  _ can I  _ and  _ may I _ all over again. It’s pretty fucked up how much Raphael’s behavior is turning him on.

Simon scoots closer, straddling Raphael’s thighs and gripping his shoulders for balance. “Would you please just do it?”

Raphael touches a thumb to Simon’s lower lip and strokes gently. “I should make you ask nicely,” he says, but he doesn’t. He unscrews the lube and pours a generous amount in his hand. He doesn’t break eye contact as he strokes himself and Simon whimpers at the sound of Raphael’s breath hitching. “Sit on it.”

It’s a lot less sexy to hear in real life but Simon will take it. He pushes up onto his knees and scoots closer still, his spent cock pressing against Raphael’s abs. Simon really doesn’t know how to do this. He digs his fingers into Raphael’s shoulders and tries not to tremble. “Master.”

Sighing softly, Raphael squeezes Simon’s hip with one hand and holds his cock still with the other. It presses against the crease of Simon’s ass, alarmingly solid. He guides the head of it to Simon’s rim but he doesn’t push up. Raphael squeezes Simon’s hip, almost reassuringly. “Sit on it,” he says again, softer this time.

“There’s no rush, Simon,” Isabelle says. “Don’t take more than you can handle. The first few inches are going to be the worst.”

Simon can feel the laughter bubbling in his chest, a byproduct of the nervous energy bubbling in his system, but he bites his tongue. He’s pretty sure they would think he was hysterical and call this off. He has to close his eyes to escape the intense look in Raphael’s and he trembles.

“Simon,” Raphael says quietly. “Color?”

For a long time, Simon doesn’t trust himself to speak. “Green,” he says, voice trembling. He wraps his arms around Raphael’s shoulder and hides his face in the sweaty skin of his neck. Raphael smells so much better than his cologne. “I’ve just never - it’s intimidating.”

Raphael moves his hand from Simon’s hip to stroke down his spine slowly. He whispers praises softly, just for Simon, but half the words are lost in translation. Still, it’s nice. It’s oddly soothing, even.

“Okay,” Simon says. He presses an open mouthed kiss to the side of Raphael’s neck and gives in to the trembling of his thighs. He sinks his weight down just enough for Raphael’s cock to breach him and Simon’s breath catches in his throat. “Oh, fuck.”

“Pet,” Raphael says. His breath hitches as Simon clenches desperately around his cock head but he doesn’t rock up or demand more. He grabs Simon’s hips with both hands and nips his shoulder. “ _ Dios _ ,” he curses, digging his nails in tight. “Should have used another finger.”

“What does he feel like, Simon?” Isabelle asks. The sound of her voice startles him and Simon clenches his eyes tighter shut. He can’t look at her right now or he risks losing focus. She sounds equal parts awed and jealous. “You should see what you look like stretched around his cock.”

“He’s - ah - big,” Simon says. He lowers himself a little more and groans. He agrees with Raphael, they definitely should have tried for another finger. Maybe skipped taking it up the ass at all tonight, but now that they’ve started, Simon doesn’t want it to stop. He can do this. He wants to do this. “Feels okay, I think. Doesn’t really hurt as much as I thought it would?”

It doesn’t, truly. He feels like he’s being stretched and stuffed and he’s barely even begun his descent onto Raphael’s length, but it’s not  _ bad _ . He can see why guys like Alec would want to do this, especially once the prostate gets involved. Simon has heard so many things. His thighs are trembling from holding himself up and he can feel the sweat dripping down the small of his back but he feels pretty damn good.

“He is pretty big for a first fuck,” Isabelle agrees. “I have toys smaller than him that I normally use for the first time experience.”

“It doesn’t surprise me that you like to fuck people in the ass,” Raphael says. He laughs softly against Simon’s shoulder and squeezes his hips. His teeth scrape lightly against Simon’s skin and he starts to work a hickey into the side of his neck. “Maybe you should have had her first.”

“Next time,” Simon says breathlessly. Even with all the slick lube between them, it burns when Simon lifts his hips up and sinks back down. It tingles and makes the room reek of strawberries, but there is a definite burn that Simon could get used to. He lets gravity and his own weight do the rest of the work, giving up on his trembling thighs and sinking the rest of the way down Raphael’s length.

It was a mistake. He feels like the air is being punched out of his lungs as soon as his ass is flush with Raphael’s hips but Christ is it a wonderful feeling. He feels so unbelievably full in a way he can’t begin to describe. Simon’s breath hitches in his throat, shuddering, but Raphael distracts him with neck kisses and nips and Isabelle curses softly in Spanish.

“Holy fuck,” Simon says, letting his head roll back. He tries to push back up to sink down again, but his thighs aren’t having it. He’s done. He is so done. He feels like he’s being stretched wider than he can handle, Raphael’s cock deeper inside of him than anything has any right to be.

Simon’s traitorous cock is starting to swell between their stomachs again and he hasn’t even touched it since he came all over the sheets. He’s starting to think he’s maybe a little more than bicurious if he’s getting off on being stuffed like this. “I’m sorry, Raphael, Master, I can’t - “

Raphael’s lips freeze where they’re tasting his skin. “Do you need to stop?”

“Oh God no,” Simon says, laughing desperately. He shakes his head and grips at Raphael’s shoulders again. He licks his lips and wonder when they got so dry. “I think my legs gave out.”

Raphael actually looks relieved. He kisses Simon’s jaw, the murmured  _ idiota _ obvious without the three years of high school Spanish. He presses up, grinding his cock against Simon in short, jerky movements, and sighs. “I can’t fuck you like this.”

“I’m sorry,” Simon says. He wants to kiss Raphael but he’s not sure if he’s allowed to. The closest he’s gotten to being kissed all night was Isabelle and even her red lips hadn’t made it to Simon’s own. He wonders if kissing is a thing you just don’t do in threesomes. Twosomes with a voyeur. Fuck if Simon knows what this is anymore.

Digging his fingers into Simon’s ass, Raphael does  _ something _ that ends up with Simon on his back before he can even blink. He feels empty, ass clenching around nothing, but Raphael is covering Simon’s body with his own and pushing right back inside of him. He doesn’t stop until he’s buried deep, his forearms trembling as he holds himself up.

“Color,” Raphael says again, like he didn’t just drop Simon on his back with every intent of fucking him senseless.

He takes this consent thing seriously and Simon wonders exactly how far off the BDSM deep end they’re going tonight. He’s excited to find out.

“Green,” Simon says again. He grips Raphael’s biceps and is distracted by the solid feel of his muscle. Raphael’s body is like pure wet dream perfection and Simon feels so soft and flabby beneath him. Why Raphael even wants SImon is beyond him. “How often do you work out?”

“Whenever I can’t sleep,” Raphael says. He sounds distracted, like maybe being buried inside of Simon is taking more out of them then he would admit. He sits up a little straighter and pumps into Simon with a short, shallow thrust.

“Which is often,” Simon guesses. His breath is caught in his lungs but it’s a wonderful feeling. He lolls his head to the side to avoid Raphael’s intense gaze and it leaves his neck open for more quick nips.

Isabelle’s gaze is just as dark and hungry as Raphael’s is. She has one knee hooked over the arm of the chair and her panties are hooked around her ankle. She’s not smooth shaven like the girls in porn always are and Simon thinks he likes that more. “You like to watch, Simon? Or do you just need distracted?”

Simon doesn’t have a clue, but he doesn’t think Isabelle was expecting an honest response. She spreads her lips with two fingers and even from a few away he can see how wet she’s gotten just from watching the two of them. He wonders what she tastes like and if she really can get off just from watching Simon get fucked.

She starts stroking herself slowly and Raphael uses Simon’s distraction to pull out and rock back in. “Oh, look at the way he bites his lips. So precious.”

Raphael does it again and Simon pants heavily. He can’t fight the soft whines from escaping his throat with every slow drag and thrust back inside of him. He tries to dig his heels into the bed to have some leverage to rock back against Raphael’s cock, but his body is betraying him. He shouldn’t be this overexerted after one orgasm and a few new sensations.

“Master,” Simon chokes out, tearing his gaze from Isabelle’s slick fingers to stare up at Raphael. “You can, ah, maybe?” Now that he wants to say them, the words die on his tongue. It’s embarrassing. He’s never been good at this dirty talk thing. Maureen likes it best when they don’t talk at all. “Harder?” Simon squeaks. “Please?”

Raphael hums, but his look of concentration doesn’t falter. He digs his fingers in the back of Simon’s thigh, pressing it back towards Simon’s chest and thrusts harder. He can’t get as deep, fucking Simon this way, but his thrusts are powerful and Simon makes choked off noises each time Raphael slides inside of him.

“Bossy,” Raphael says, bracing his hand on Simon’s chest. He doesn’t seem to mind and it doesn’t slow his roll any. The wonderful, just the right side of painful roll that has his cock nearly splitting Simon in two with each sharp roll of his hips. His palm slips against Simon’s skin, and he presses down harder.

“Careful,” Isabelle warns, her breath hitching. She has two fingers inside of herself and Simon idly wonders if her acrylic nails hurt or if it’s the same good kind of pain as getting fucked.

There’s an exchange in Spanish but Simon doesn’t care if they’re insulting each other or trading recipes. He closes his eyes and squeezes his ass around Raphael’s cock weakly. It feels good, clenching around him, and Simon wonders if it feels as good for Raphael. It’s hard to tell when Raphael’s breath is already desperate and shallow as he fucks Simon hard.

The hand on Simon’s chest slips to his throat, fingers curling but applying no pressure. It makes Simon’s cock throb hard against his stomach and he can feel the weak spurt of precome in his happy trail. Simon moans and curls his fingers around Raphael’s wrist, keeping his hand exactly where it is.

“Raphael!” Isabelle says. She sounds  _ mad _ and Simon’s eyes snap open but he can’t roll his his head to look at her when Raphael’s fingers are curled around his throat. “I was teasing about choking him!”

“I’m not,” Raphael says, huffing. He flexes his fingers, as if to prove a point, and Simon whines. There’s barely any pressure on his throat at all and Simon finds himself desperate to find out what it would feel like. 

“You could,” Simon babbles. “You could totally choke me.”

“That’s the kind of thing that needs to be negotiated  _ before _ the throes of passion,” Isabelle says. She looks hesitant, like she’s not sure if she should put a stop to this. Like maybe Raphael really shouldn’t be choking Simon.

But it feels  _ good _ , especially when Raphael applies a little more pressure to this throat. Not enough to cut off airflow but enough to make it a little harder to catch his breath. The sharp snapping of Raphael’s hips doesn’t falter and Simon finds himself begging for  _ more. _

“Please, Master,” Simon sobs. His body is wracked with it, fire burning in his veins and tension bubbling away just under the surface. He’s so close to coming, again, and he hasn’t even touched himself. It’s the hard drag of Raphael’s cock inside of him, barely grazing against his prostate, and the gentle pressure on his throat. “Choke me.”

“Simon,” Isabelle says, breathless. Her hips rock up into the desperate rubbing of her fingers.

Raphael’s fingers curl tighter around Simon’s throat, sharp enough that he has to gasp for air. It’s going to leave a ring of bruises in the morning but Simon can't bring himself to care. He’s lightheaded and he can’t focus. When he thinks he’s going to faint, Raphael’s grip slackens and Simon sucks in sharp breathes and digs his nails into Raphael’s wrist. 

He can feel his body squirming, arching up into Raphael’s touch and clenching around his cock, but there is a disconnect. He squeezes Raphael’s wrist, asking quietly, and Raphael presses down again, harder this time. It doesn’t take as long for Simon’s vision to go blurry this time, white hot pressure nearly blinding.

Distinctly, Simon registers that he’s coming. It tingles in the base of his spine, cock throbbing, but it’s nothing compared to the way he’s gasping for air that he’s just not getting. Simon never wants it to stop.

Letting go of Raphael’s wrist has him immediately slackening his grip on Simon’s throat. He moves his hand to the bedspread and he looks down at Simon with what Simon is pretty sure is actually  _ concern _ . His hips have stopped moving. Raphael swears at himself in Spanish and Simon just reaches for his wrist, holding on.

“Green,” Simon says, breathless. He’s not sure the sound comes out at all, because Raphael just stares down at him in wonder. He licks his lips and chokes the word out again. “ _ Green. _ ”

“Fuck,” Isabelle says with a choked off noise. She exists just outside of his peripherals but Simon can’t bring her into focus. He can tell she’s rubbing desperately at her clit, hips pushing up into the touch, but it’s not registering in his brain. Her thighs are sticky with her own slick.

“Dios, Pet, I’m sorry,” Raphael says. He pulls out but before Simon can object, he flips Simon onto his stomach and pushes his thighs apart wide. Immediately, he slides back into Simon with a hard, desperate thrust, and presses a wet kiss to the back of Simon’s neck. “ _ Lo siento, dios, perdóname. _ ”

Raphael fucks him hard and fast, barely pulling out all the way before slamming back in. The sound his hips make hitting Simon’s ass is loud to Simon’s ears, even more so than the harsh sound of Raphael’s breathing and the litany of apologies. He covers Simon’s body with his own, smothering him, and he comes with a choked sound and his teeth buried in Simon’s shoulder.

The bite aches but it’s a dull pain compared to everything else. Simon thinks he likes that, too.

“Are you okay, Simon?” Isabelle asks. She pulls her dress down over her hips and crouches by the side of the bed. Her fingers brush his sweaty hair from his forehead and she looks actually concerned. “Oh god, we should not have let it get that far. Do you want to go to the hospital?”

“Hospital?” Simon asks, tiredly. She means for the choking, he realizes. She’s worried he might have brain damage. Simon smiles despite himself and closes his eyes. “No, I’m good. I am so good right now.”

Raphael rolls off of Simon’s back and off the bed altogether. He says something in Spanish, something Simon can’t translate, and Simon watches him head towards the bathroom. He should be upset, he thinks, or maybe insulted.

Simon tells himself Raphael is probably just going to flush the condom and he tries not to miss the warmth of his body too much.

“Shhh,” Isabelle says. She strokes her fingers through Simon’s hair and smiles reassuringly. “He’s just going to clean up.”

That makes since, Simon figures. He should probably do that, too, but he doesn’t think any of the muscles are working in his body right now. He wonders if he’ll choke to death if the tries to sleep like this. “Did you want me to - ?”

At first, Isabelle is confused. When realization dawns, her expression softens. She kisses his forehead softly. “Maybe in the morning, if you feel up to it. Go ahead and rest for now.”

Simon wants to object, he really does. He’s pretty sure there is a laundry list of things they need to talk about. Not just Simon and Isabelle, but Raphael too. Like where the hell the kinky shit came from and if they can do it again soon. Maybe Isabelle can be more closely involved next time. Simon would be okay with that.

Isabelle’s fingers are gentle on his scalp though, rubbing reassuring patterns through his hair, and Simon can’t help but drift off.

 

* * *

Simon comes to to Raphael rolling him over and helping him sit up and Isabelle pressing an ice cube against his chapped lips. He shivers and leans back into Raphael’s body and startles when he realizes Raphael is dressed. “You’re leaving?” His voice is scratchy and Simon doesn’t recognize himself.

“I had to get ice,” Raphael says. His arm is around Simon’s waist, holding him steady, and his fingers stroke Simon’s lower belly gently. “Relax.”

This time, Simon is expecting the touch of the ice cube to his lips. It’s soothing and he sighs, letting it happen as he closes his eyes. Next is a cold compress, pressed against his throat, and it’s a welcome relief that Simon didn’t even know he needed.

“Do you want to try to take a bath tonight?” Isabelle asks. She’s so soothing and gentle, the complete opposite of the girl who convinced them into this situation in the first place. “It might make you sleep better.”

Simon wants to say he’s pretty sure he could pass the fuck out right now, but it hurts to speak and he’s sure they both know it, anyway. He rolls his head against Raphael's shoulder and tries not to wince when he sighs heavily. In hindsight, the choking was probably a terrible idea. He has no idea how he’s going to explain this to his mom or Clary. Isabelle was right, of course.

“At least wait to get under the covers before you fall asleep,” Raphael murmurs in Simon’s ear. He doesn’t move to pull back the soiled cover though and Simon has no intention of moving from where he’s pressed heavily into Raphael’s side. He’s pretty sure this is exactly where he wants to be.

“I think he’s out again,” Isabelle says softly, and she’s not entirely wrong.

 

* * *

His voice hasn’t returned by the morning. His voice cracks when he tries to speak and he’s silenced by the soft press of Isabelle’s lips. Her body is so warm and soft that it takes Simon a moment to realize that Raphael is still in bed, too, pressed up behind Simon with a possessive arm around his waist.

“I think we’re going to have to rain check the cunnilingus,” Isabelle says, pressing her finger to Simon’s lips. “If you’re up for it.”

Simon is. He definitely is. His voice croaks but she shushes him before he gets the chance to say anything. He wants her. He wants to take care of her. He doesn’t want to wait for this proverbial next time that may or may not happen.

Isabelle must know what he wants, because she tugs his hand between her thighs and shoves his fingers into her lacey panties. Her folds are warm and soft and the lace scratches the back of his wrist and the sensations are amazing. She’s already starting to get slick and Simon spreads it over her clit slowly. He’s no better at this than he is giving head, but he wants to be. He likes the way Isabelle’s breath hitches and she rocks against his fingers.

“Insatiable,” Raphael murmurs against Simon’s shoulder, though he has no idea which one of them Raphael means. Simon’s pretty sure he can feel Raphael smiling against his naked skin, even as he presses the length of his cock against the crase of Simon’s ass.

And  _ Oh _ , Simon thinks. That’s definitely a thing that happened last night and maybe it’s a thing that could happen again, too. He presses his hips back, experimentally, and Raphael grinds against his ass. It feels good in a way Simon can’t begin to explain.

After,  when Raphael has come sticky and hot in the small of Simon’s back and Isabelle’s cunt pulses around his fingers, hips grinding into the palm of his hand, they return the favor. Isabelle’s fingers curl around Simon’s leaking cock, small and delicate, while Raphael’s fingers curl loosely around his throat.

This time, there's no pressure cutting off his breathing, but Raphael nips his lower lip and kisses him for the first time and it has the same effect.


End file.
